Treeloft Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to €185 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Where to stay in Treeloft

Find the best Treeloft areas and neighborhoods for the activities you enjoy most. Learn more about Treeloft
Default Image

Chestnut Springs

While Chestnut Springs may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Wintergreen Resort and Raven's Roost Overlook.

Find hotels in Chestnut Springs

Top hotels in Treeloft

Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
Wintergreen Resort
9.8/10 Exceptional! (132 reviews)
Well worth it - 10/10
"My family and I stayed here for a long weekend to make the most of some local hikes, end of season snow on the slopes and quality time together. The property met all of our needs and wants when we were browsing for availabilities. We had a hiccup accessing the property during initial check in (key ..."

Reviewed on 16 Mar 2025

Get rates
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
Wingate by Wyndham Waynesboro
Wingate by Wyndham Waynesboro
2.5 out of 5
20 Windigrove Dr, Waynesboro, VA
8.4/10 Very Good! (821 reviews)
"The breakfast was terrible.My husband said it was the worse breakfast ever. We were in a non smoking room but housekeeping was across the hall and we could snell smoke. The shower was good and the towels were very nice"

Reviewed on 10 Apr 2025

Get rates
Wingate by Wyndham Waynesboro
Hotel 24 South
Hotel 24 South
3 out of 5
24 South Market Street, Staunton, VA
Fully refundableReserve now, pay when you stay
The price is €109 per night from 12 May to 13 May
€109
includes taxes & fees
12 May - 13 May
9.4/10 Exceptional! (1,003 reviews)
"Lovely place to stay in Staunton, however all rooms are not equal, so pay attention when booking. A king room varies in size, and amenities such as a mini frig are not guaranteed room to room."

Reviewed on 8 Apr 2025

Hotel 24 South
See all 1,149 properties in Treeloft
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Treeloft holiday package cost?
Perhaps less than you imagined — from as low as , actually! By combining hotels, flights and car rentals into your own tailor-made package, your Treeloft escape is just a few clicks away.
How do I get a cheap travel package to Treeloft?
Our Treeloft holiday packages offer plenty of savings for the savvy explorer. For the best deal, simply combine your flights, hotels and extras (including tours) into a budget-friendly package. But low prices are only the start of your next awesome adventure. When you book with Expedia, you’ll have more than 550 air carriers and 1,000,000 hotel options worldwide to select from. Whatever your style, there’s a package here just for you.
Where should I stay in Treeloft?
If you plan to check out Wintergreen Resort, give commuting a miss and find someplace to stay close by. It’s one of the most popular attractions in Treeloft.
What are the top hotels in Treeloft?
Get your escape off to a good start by reserving a room at Custom Builder Just Completely Remodeled This Mountain Chalet. . . With Hot Tub. It’s one of most popular hotels in Treeloft. Another option is Wintergreen Resort Home With 2 Decks + Ski Access.
How far in advance should I book my Treeloft holiday?
While prices do change, we generally recommend booking your seats as early as possible. Many international airfares are found on Expedia up to a year in advance. If circumstances have left you booking last minute, you might still be lucky. Discount prices to Treeloft sometimes emerge only weeks before departure.
What does an Expedia Treeloft travel package include?
Expedia has all you need to plan your Treeloft escape, but how your package is structured is up to you. Select from any combination of hotels, rental cars and flights. Looking for some activities to keep you on the go? Once you’ve made your booking, you can add them on too. Whatever your budget or style, there’s a deal to meet your needs.
What should I know before booking a Treeloft travel package?
We already have low prices. However, you’ll enjoy even more bargains if you book your hotels, flights and car rentals together. With an Expedia travel package, you’ll always get transparent pricing and tons of choice.
Can I choose my airline with a Treeloft Expedia holiday package?
Yes, the choice is all yours. Expedia has access to more than 550 airlines globally, so you can customize your Treeloft holiday according to your travel preferences.
If I'm not able to travel, can I cancel my Treeloft holiday package?
Whether it’s your hotel or flight, you can cancel or alter it. Locked in your Treeloft holiday package in the last 24 hours? You may be able to make changes at no cost. For bookings older than that, you may be charged a fee by your airline, hotel or car rental company. For more details, head to our Customer Service Portal. We’ll help you each step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.